This invention provides dithioethers of 2-phenyl-2-alkenals defined according to the structure: ##STR3## wherein N represents 0 or 1 and each of R.sub.4 and R.sub.5 represent hydrogen or methyl taken alone or taken in admixture with compounds defined according to the structure: ##STR4## wherein N, R.sub.4 and R.sub.5 are defined, supra and uses thereof in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes and medicinal products.
Artificial flavoring agents for foodstuffs have received increasing attention in recent years. In many areas, such food flavoring agents are preferred over natural flavoring agents at least in part because of the uniform flavor that may be so obtained. For example, natural food flavoring agents such as extracts, essences, concentrates and the like are often subject to wide variation due to changes in the quality, type and treatment of the raw materials. Such variations can be reflected in the end product and result in unreliable flavor characteristics and uncertainty as to consumer acceptance and cost. Additionally, the presence of the natural product in the ultimate food may be undesirable because of the increased tendency to spoil. This is particularly troublesome in convenience and snack food usage where such products as dips, soups, chips, prepared dinners, canned foods, sauces, gravies and the like are apt to be stored by the consumer for some time prior to use.
The fundamental problem in preparing artificial flavoring agents is that of achieving as nearly as possible a true flavor reproduction. This generally proves to be a difficult task since the mechanism for flavoring development in many foods is not understood. This is notable in products having sauted onion, garlic and hydrolyzed vegetable protein-like flavors.
Reproduction of black cherry, grape, tropical fruit, sauted onion, garlic, cocoa, cabbage and hydrolyzed vegetable protein-like aroma and taste nuances for use in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes and/or medicinal products has been the subject of a long and continuous search by those engaged in the production of foodstuffs, chewing gums, toothpastes and medicinal products. The severe shortage of foods, world-wide especially proteinaceous foods in many parts of the world has given rise to the need for utilizing non-meat sources for proteins and making such proteins as palatable and as meat-like as possible. Hence, materials which will closely simulate or exactly reproduce flavor and aromas of meat-like substances including hydrolyzed vegetable protein-like, and sauted onion-like flavors are required. Furthermore, meat flavors have been previously enhanced by the use of such materials as monosodium glutamate. In many diets, sodium is not desired. In many other diets, monosodium glutamate is not desired. Therefore a need has arisen for a monosodium glutamate replacer.
In general, a need exists for the preparation of black cherry, grape, tropical fruit, sauted onion, garlic, cocoa, cabbage-like and hydrolyzed vegetable protein-like aroma and taste nuances for black cherry, grape, tropical fruit, sauted onion, spice, garlic, vegetable and hydrolyzed vegetable protein flavored foodstuffs, chewing gums, toothpastes and medicinal products.
Dialkyl mercaptals are known in the prior art for augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes and medicinal products.
Thus, U.S. Pat. No. 4,481,224 issued on Nov. 6, 1984 discloses alkylthioalkanal dialkyl mercaptals defined according to the structure: ##STR5## wherein n is an integer of from 1 up to 3; and wherein R.sub.1 and R.sub.2 are the same or different C.sub.1 -C.sub.3 alkyl. It is disclosed in U.S. Pat. No. 4,481,224 that such dialkyl mercaptals are useful in augmenting or enhancing the aroma or taste of various fruit, vegetable, cheese, tuna fish and hydrolyzed vegetable protein-like flavors.
2-(2,6-dimethyl-1,5-heptadienyl)-1,3-dithiolanes defined according to the generic structure: ##STR6## wherein R.sub.1 and R.sub.2 are the same or different and each represents methyl or hydrogen with the proviso that at least one of R.sub.1 and R.sub.2 is methyl is disclosed for its uses in augmenting or enhancing the aroma or taste of foodstuffs in U.S. Pat. No. 4,464,408 issued on Aug. 7, 1984. Such 2-(2,6-dimethyl-1,5-heptadienyl)-1,3-dithiolanes are disclosed in U.S. Pat. No. 4,464,408 to augment or enhance the aroma or taste of cooked liver, liverwurst and rare liver flavored foodstuffs.
Acetals of phenyl alkenals are disclosed for augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes and medicinal products in the prior art, particularly in U.S. Pat. No. 3,908,023. Thus, U.S. Pat. No. 3,908,023 issued on Sept. 25, 1975 discloses the use of the genus of compounds defined according to the structure: ##STR7## for augmenting or enhancing the aroma or taste of foodstuffs particularly chocolate and cinnamon flavored foodstuffs (wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond; wherein R.sub.2 and R.sub.3 each represents methyl or ethyl; or R.sub.2 and R.sub.3 taken together represents ethylene; wherein when the dashed line at the "4,5" position is a double bond n is 2, m is 1 and p is 1; wherein when the dashed line at the "3,4" position is a double bond, n is 3, m is 1 and p is 0.
Specific examples of compounds falling within the structure of U.S. Pat. No. 3,908,023 are as follows: ##STR8##
3-Phenyl pentenals have been suggested in U.S. Pat. No. 3,694,232 for use in cocoa flavors whereby notes characteristic of milk chocolate are provided. 3-Phenyl-4-pentenal is indicated to cause the chocolate beverage to have a fuller, richer sweet milk chocolate flavor. U.S. Pat. No. 3,582,360 issued on June 1, 1971 discloses certain 2-phenyl-2-alkenals (the dithio acetals for which are part of the instant invention) as being useful for preparing flavoring compositions and food compositions, particularly those having chocolate or cocoa flavors and/or aroma qualities. Thus, for example, the compound 5-methyl-2-phenyl-2-hexenal having the structure: ##STR9## is indicated therein to alter imitation cocoa flavor so as to provide a more natural cocoa flavor and impart the character of bitter chocolate. Other phenyl alkenals disclosed for use in chocolate flavors in U.S. Pat. No. 3,582,360 are those having the structures: ##STR10##
Cinnamaldehyde diethyl acetal is reported in "Perfume and Flavor Chemicals (Aroma Chemicals)" by S. Arctander (published in 1969) as having a "faint but fresh, green, slightly spicy, oily, sweet odor and a mild and oily sweet taste". Arctander goes on to state: "since this acetal-like most other acetals-is unstable under mildly acid conditions, it finds little if any use in flavor compositions".
The dithioethers of 2-phenyl-2-alkenals of our invention have unexpected, unobvious and advantageous properties in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes and medicinal products compared to the relevant compounds of the prior art.